Enzymatic synthesis of l-menthyl esters in organic solvent-free system
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- Shimada, Y., Hirota, Y., Baba, T. et al. J Am Oil Chem Soc (1999) 76: 1139. doi:10.1007/s11746-999-0086-3
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l-Menthol has been widely used as a food additive and an ingredient of cosmetics, and it is esterified to moderate the strong flavor. We attempted esterification of l-menthol with long-chain unsaturated fatty acid in an organic solvent-free enzymatic system. Commercially available lipases were screened, and Candida rugosa lipase was selected as a catalyst. Several factors affecting the esterification were investigated, and the reaction conditions were determined as follows: A reaction mixture of l-menthol/fatty acid (1:3, mol/mol), 30% water, and 700 units of the lipase per gram of reaction mixture was incubated at 30°C with stirring. After 24 h under these conditions, the esterification extents of l-menthol with oleic, linoleic, and α-linolenic acids reached 96, 88, and 95%, respectively. The structure of the esterified product was confirmed by mass, infrared, and nuclear magnetic resonance spectroscopies. Bacause Candida lipase acted strongly on l-menthol and very weakly on d-menthol, dl-menthol was esterified with oleic acid under the same conditions. The reaction showed high enantioselectivity; the enantiomeric ratio (E) was 31, and enantiomeric excess (ee) of l-menthyl oleate reached 88% after 32 h.